Реакция #6992

Уравнение реакции

5-bromo-2-(3,4-dichlorophenoxy)-benzaldehyde

DMF

→

title product

5-CYANO-2-(3,4-DICHLOROPHENOXY)-BENZALDEHYDE

Условия реакции

Обработка

1. 1
   ДругоеUnder N2 in a flame-dried 3-neck round bottomed flask fitted with a reflux condenser and magnetic stirrer
2. 2
   Другоеwhile degassing with N2 for 5 min
3. 3
   ТемператураAfter heating at approximately 80° C. for 90 min.
4. 4
   Температураto cool to room temperature
5. 5
   workup.ADDITIONThe reaction mixture was then diluted with water and ethyl acetate (EA)
6. 6
   workup.STIRRINGstirred another 10 min
7. 7
   ДругоеThe water layer was separated
8. 8
   Экстракцияextracted twice with EA
9. 9
   Промывкаwashed with an aqueous solution of Rochelle salt (potassium sodium tartrate tetrahydrate)
10. 10
    СушкаThe organic layer was dried with Na2SO4
11. 11
    Фильтрацияfiltered
12. 12
    Концентрированиеconcentrated in vacuo to an oil
13. 13
    Другоеchromatographed on a 15×5 cm column of silica gel
14. 14
    Промывкаeluting with CH2Cl2:hexanes (1:1)

Методика

Under N2 in a flame-dried 3-neck round bottomed flask fitted with a reflux condenser and magnetic stirrer, a mixture of 5-bromo-2-(3,4-dichlorophenoxy)-benzaldehyde (3.0 g, 8.7 mmol), zinc (II) cyanide (1.5 g, 13 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.5 g, 1.3 mmol) in anhydrous DMF (145 ml) was stirred at room temperature while degassing with N2 for 5 min. After heating at approximately 80° C. for 90 min., the reaction was judged complete by thin layer chromatography (50% CH2Cl2:hexanes) and was allowed to cool to room temperature. The reaction mixture was then diluted with water and ethyl acetate (EA) and stirred another 10 min. The water layer was separated, extracted twice with EA and combined with the original EA layer, and washed with an aqueous solution of Rochelle salt (potassium sodium tartrate tetrahydrate) followed by aqueous NaCl. The organic layer was dried with Na2SO4, filtered and concentrated in vacuo to an oil. The oil was flash chromatographed on a 15×5 cm column of silica gel, eluting with CH2Cl2:hexanes (1:1) to obtain the title product as a white solid, 1.5 g (60%), m.p. 122–126° C.

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